Water → Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]methylamino]methyl]benzoate

HRID 1633846Notes

Reaction equation

HRID 1633846 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][NH:16][CH3:17].[CH2:18]([O:25][C:26]([NH:28][C@@H:29]([C:32](O)=[O:33])[CH2:30][OH:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1C=CC2N(O)N=NC=2C=1.O.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C.C(Cl)Cl>[F:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:11])([CH3:12])[CH3:10])=[O:7])=[CH:4][C:3]=1[CH2:15][NH:16][CH2:17][C:30](=[O:31])[C@@H:29]([CH2:32][OH:33])[NH:28][C:26]([O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:27]

Participants

7

Reactant 5

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 489184Z-D-Ser-OHHCID 117912751,1-Dimethylethyl 4-fluoro-3-[(methylamino)methyl]benzoate

Product 1

HCID 131723730Tert-butyl (r)-4-fluoro-3-[[[n-(benzyloxycarbonyl)serinyl]methylamino]methyl]benzoateYield 85.8%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

According to the procedure of Preparation 4(c), except using tert-butyl 4-fluoro-3-(methylaminomethyl)benzoate (4.00 g, 16.7 mmole), N-(benzyloxycarbonyl)-D-serine (4.00 g, 16.7 mmole), HOBt.H2O (2.3 g, 17 mmole), DCC (2.4 g, 11.6 mmole), and 1:1 DMF/CH2Cl2 (100 mL), the title compound (6.60 g, 79%) was prepared as a sticky foam following flash chromatography on silica gel (50% EtOAc/hexanes): MS (ES) m/e 461.1 (M+H)+.

Sources & evidence

ORD record
ord-b5975a095c5c4ae39efb7cd8c1aed1ae
Source dataset
uspto-grants-2003_01
Patent number
US06503903B1

Reaction notes

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